Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization.
The first total synthesis of the natural nondimerizing o-quinol (+)-wasabidienone B1 was achieved from commercially available 1,3,5-trimethoxybenzene. The key dearomatizing transformation was efficiently accomplished via a hydroxylative phenol dearomatization reaction using the stabilized lambda(5)-iodane reagent IBX (SIBX). (+)-Wasabidienone B1 was then converted into its congener (-)-wasabidienone B0 via an improved thermally induced ring-contracting isomerization reaction.
Pouységu
Laurent
L
Institut des Sciences Moléculaires, CNRS-UMR 5255, Université de Bordeaux, Pessac Cedex, France.
Marguerit
Mélanie
M
Gagnepain
Julien
J
Lyvinec
Gildas
G
Eatherton
Andrew J
AJ
Quideau
Stéphane
S
D002384:Catalysis; D006900:Hydroxylation; D007202:Indicators and Reagents / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D007536:Isomerism; D007783:Lactones / Q000138:chemical synthesis*; D010636:Phenols / Q000737:chemistry*; D011809:Quinones / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D007462:Iodobenzenes; D007783:Lactones; D010636:Phenols; D011809:Quinones; C533651:wasabidienone B0; C533650:wasabidienone B1; C476101:o-iodoxybenzoic acid